Hydrochloric Acid → HCID 11819383, compound
Reaction equation
[NH:1]([CH2:3][C:4]([OH:6])=[O:5])[CH3:2].[Cl:7][CH2:8][C:9](Cl)=[O:10].Cl.[Cl-].[Na+]>[OH-].[Na+]>[Cl:7][CH2:8][C:9]([N:1]([CH2:3][C:4]([OH:6])=[O:5])[CH3:2])=[O:10]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -5 °C
Procedure
Sarcosine (32.38 g, 363 mmol) was dissolved in 90 mL 4N aqueous sodium hydroxide, and cooled in an ice-salt bath to -5° C. The mixture was stirred vigorously and treated simultaneously with chloroacetyl chloride (32 mL, 402 mmol) and 110 mL 4N aqueous sodium hydroxide dropwise over 20 minutes. After warming to ambient temperature and stirring for 34 hours, the solution was carefully acidified to pH 2 (concentrated hydrochloric acid), saturated with sodium chloride, and extracted with ethyl acetate (2×400 mL). The extracts were combined, dried over anhydrous magnesium sulfate and evaporated to afford N-chloroacetylsarcosine as an oil, sufficiently pure for the next step (39.34 g, 238 mmol, 65%).
Workup
- temperatureAfter warming to ambient temperature
- stirringstirring for 34 hours
- extractionextracted with ethyl acetate (2×400 mL)
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-6d125958bce24a5b998ec66da61b1899
- Source dataset
- uspto-grants-1994_10
- Patent number
- US05358946
Reaction notes
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